Paper
meta-Photocycloaddition of trans-1,2-dichloroethene to the benzene ring: directed cyclopropane ring formation in the tricyclo[3.3.0.02,8]oct-3-ene skeleton
Published 1989 · A. Gilbert, P. Heath, P. Rodwell
Journal of The Chemical Society-perkin Transactions 1
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Abstract
1,2-trans-Dichloroethene undergoes meta-photocycloaddition to benzonitrile, the toluonitriles, benzene, phenol, the cresols, fluorobenzene, chlorobenzene, trifluoromethylbenzene, and m-trifluoromethylbenzonitrile. The arene substituents selectively direct the positions of ethene attack, but in all cases the formation of the cyclopropane ring in the tricyclo[3.3.0.02,8]oct-3-ene skeleton is specifically controlled by the ethenyl chlorine to give exclusively the 6-exo-7-endo-dichloro adduct isomer.
Meta-photocycloaddition of trans-1,2-dichloroethene to benzene ring leads to directed cyclopropane ring formation in the tricyclo[3.3.0.02,8]oct-3-ene skeleton, with ethenyl
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